Robert Lewis "Bobby" Anderson, Jr.

Robert Lewis Anderson, Jr., lovingly known as “Bobby” or “Bob Boy”, of Clements, Maryland, passed away peacefully on January 29, 2026, at Hospice House, surrounded by his loving family. He was 86 years old. Bobby was born on December 4, 1939, in Clements, Maryland, to Robert Lewis Anderson, Sr. and Lucy Mae (Hurry) Anderson. A lifelong resident of Clements, Bobby was deeply rooted in the community he loved and served so faithfully. He graduated from Margaret Brent High School in 1957 and began his working life at Hurry’s Store for his Uncle Jimmy Hurry. He later worked as a feed salesman for Bowman Brothers before returning home to the family business. Bobby spent an extraordinary 60+ years behind the bar at Anderson’s Bar in Clements, where he became much more than a bartender. He was a trusted friend, a listener, and a source of laughter and wisdom for generations of patrons. Affectionately known by many as the “Mayor of Clements”, Bobby was a true pillar of the community, always ready with a story, a smile, and a good dose of humor. On February 2, 1961, Bobby married his love, Frances Dianne (Ellis) Anderson. Together they shared 65 wonderful years of marriage, building a life centered on family, friendship, and hard work. Bobby was a devoted father to four children: Catherine Pamela Clarke (JD) of Clements, Maryland; Christina Lynn Hurst (Jim) of Clements, Maryland; Joseph Blair Anderson (Connie) of Clements, Maryland; and the late James Craig Anderson (Tara) of Clements, Maryland. Bobby was an avid supporter of the local softball community, proudly sponsoring teams throughout his career and forming many lasting friendships along the way. He also supported local shuffleboard and dart leagues, always encouraging camaraderie and community spirit. When he wasn’t at the family bar, Bobby could often be found working on his tobacco farm, a testament to his strong work ethic and love for the land. He greatly enjoyed traveling with his wife, Dianne, and dear friends, Donnie and Isabel Williams, as well as rabbit hunting with his good friends and especially his late friend, Elmer Nelson. Bobby was a devoted supporter of Sacred Heart Church, where his steadfast faith and generosity played an important role in sustaining the church community. Bobby was preceded in death by his parents, Robert and Lucy Anderson, and his beloved son, James Craig Anderson, and his grandson, Travis Andrew Davis. In addition to his wife and children, he is survived by his sister, Virginia Mae Pierce (Johnny); his cherished grandchildren, James, Leroy Pilkerton III, Caitlin Anne Clarke, Daniel Joseph Clarke, Shannon Lynn Stone, Samantha Marie Anderson, Taylor Nicole Davis, , Dustin Blair Anderson, Davey Alan Anderson, Olivia Nicole Carr, Emma Grace Anderson, and his adored great-grandchildren, Cora May Pilkerton Carson Alvey Pilkerton, Brielle Stone, and Ada Stone. The family will receive friends on Wednesday, February 11, 2026, from 5:00 PM to 8:00 PM, in the Mattingley-Gardiner Funeral Home, Leonardtown, MD. A Mass of Christian Burial will be celebrated on Thursday, February 12, 2026, at 11:00 AM in Sacred Heart Catholic Church, Bushwood, MD, with Rev. James Oberle officiating. Interment will follow at Sacred Heart Catholic Cemetery, Bushwood, MD. Pallbearers honoring Bobby’s life will be Bruce Barnes, Roy Guy, James Pilkerton III, Dusty Anderson, Davey Anderson, and Josh Piece. Honorary pallbearers will be Bill Bailey, Don Purdy, Jennings Anderson, Bert Anderson, Jamie Tennyson, Robbie Tennyson (godchild), George Gibson III, and Todd Gibson. Their presence reflects the deep friendships and family bonds that meant so much to him throughout his life. In lieu of flowers, donations may be made in Bobby’s memory to the 7th District Rescue Squad, St. Mary’s Nursing Center, Sacred Heart Catholic Church, or ACTS. Condolences may be made to the family at www.mgfh.com. Arrangements provided by the Mattingley-Gardiner Funeral Home and Cremation Services, P.A., Leonardtown, MD.